Methyl 3,5-bis(methoxymethoxy)benzoate → 3,5-Bis(methoxymethoxy)benzylalcohol

HRID 1798077Notes

Reaction equation

HRID 1798077 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:7]=[C:6]([O:14][CH2:15][O:16][CH3:17])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:13][O:12][CH2:11][O:10][C:8]1[CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=[C:6]([O:14][CH2:15][O:16][CH3:17])[CH:7]=1

Participants

4

Reactant 2

HCID 10106435Methyl 3,5-bis(methoxymethoxy)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 104437513,5-Bis(methoxymethoxy)benzylalcoholYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3,5-bis-methoxymethoxybenzoic acid methyl ester (11.1 g, 43.3 mmol) in Et2O (150 mL) was treated with LiAlH4 (2.46 g, 65.0 mmol) at 0° C. The suspension was stirred at room temperature for 1 h. The reaction mixture was slowly quenched by water and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=2:3) to afford the title compound (9.16 g, 93%). 1H NMR (300 MHz, CDCl3) δ 6.71 (s, 1H), 6.70 (s, 1H), 6.64 (s, 1H), 5.15 (s, 4H), 4.62 (d, J=6.0 Hz, 2H), 3.47 (s, 6H), 1.93 (t, 1H).

Workup

  1. customThe reaction mixture was slowly quenched by water
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=2:3)

Sources & evidence

ORD record
ord-cd724ba28c784d8e8fa56f96a9acb67e
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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